2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid

• ChemBase ID: 102931
• Molecular Formular: C9H10O5
• Molecular Mass: 198.1727
• Monoisotopic Mass: 198.05282342
• SMILES: COc1c(O)ccc(c1)C(O)C(=O)O
• Canonical SMILES: COc1cc(ccc1O)C(C(=O)O)O
• InChI: InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)
• InChIKey: CGQCWMIAEPEHNQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
• IUPAC Traditional name: vanillylmandelic acid; 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid
• Synonyms: Vanillylmandelic acid; α,4-Dihydroxy-3-methoxybenzeneacetic acid; VMA; Vanilmandelic acid; Vanillomandelic acid; DL-4-HYDROXY-3-METHOXYMANDELIC ACID; 4-HYDROXY-3-METHOXYMANDELIC ACID; DL-4-Hydroxy-3-methoxymandelic acid; α,4-Dihydroxy-3-methoxybenzeneacetic acid; Vanillylmandelic acid; 4-Hydroxy-3-methoxy-DL-mandelic acid; Vanillylmandelic acid; (+/-)-Vanilmandelic Acid; (4-Hydroxy-3-methoxyphenyl)glycolic Acid; 3-Methoxy-4-hydroxyphenylhydroxyacetic Acid; HMMA; Vanilinmandelic Acid; dl-Vanillomandelic Acid; 3-甲氧基-4-羟基扁桃酸; 4-羟基-3-甲氧基扁桃酸; 4-羟基-3-甲氧基苦杏仁酸; 香草扁桃酸; DL-4-羟基-3-甲氧基扁桃酸; 4-羟基-3-甲氧基-DL-扁桃酸

Database IDs

• CAS Number: 2394-20-9; 55-10-7
• EC Number: 200-224-0
• MDL Number: MFCD00004235
• Beilstein Number: 2213227
• PubChem SID: 162090650; 24277743
• PubChem CID: 1245
• CHEBI ID: 20106
• Chemspider ID: 1207
• MeSH Name: Vanilmandelic+acid
• Wikipedia Title: Vanillylmandelic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.1136312
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9234009
• LogD (pH = 7.4): -3.0261636
• Log P: 0.43459907
• Molar Refractivity: 47.1479 cm^3
• Polarizability: 18.376032 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: Off-White to Pale Pink Solid
• Melting Point: 127-129°C (dec.); 131-133 °C; 132-134 °C (dec.)(lit.); 133-134°C dec.; 134-135

Safety Information

• Storage Condition: 2-8°C, Desiccate, Store Under Nitrogen; Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Mechanism of Action: Catecholamine metabolite

Product Information

• Purity: ≥99.0% (T); 98%
• Biological Source: Found in urine
• Application(s): Used to diagnose an adrenal gland tumor called pheochromocytoma
• Linear Formula: HOC6H3(OCH3)CH(OH)CO2H

DETAILS

MP Biomedicals - 05210657

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02105689

Crystalline
A metabolite of epinephrine.

Toronto Research Chemicals - H946330

A metabolite of catecholamines.

REFERENCES

• Canfell, P., et al.: Clin. Chem., 32, 222 (1986)
• Nunez, C., et al.: Eur. J .Clin. Chem. Clin. Biochem., 32, 461 (1986)
• Weise, M., et al.: J. Clin. Endocrinol. Metab., 87, 1955 (1986)